Total synthesis of cynaropicrin

Org Biomol Chem. 2021 Jul 21;19(27):6038-6044. doi: 10.1039/d1ob00657f. Epub 2021 May 13.

Abstract

Cynaropicrin is found in artichoke (Cynara scolymus) and is the source of its bitter taste and it is a sesquiterpene lactone with a 5-7-5 tricyclic skeleton, six chiral centers, and four exo-olefins. This natural product has numerous attractive biological activities including the inhibition of NF-κB activation, antihepatitis C activity, and antitrypanosomal activity. In this study, the first total synthesis of cynaropicrin was achieved starting from (S)-α-pinene. The synthesis involved a stereoselective Favorskii rearrangement and an indium-promoted diastereoselective Barbier reaction.

Publication types

  • Research Support, Non-U.S. Gov't